10 Most Controversial Comedians of All Time

Controversial comedy; where would we be without it? For almost a century it has been the task of new generations of comics to help us deal with social and political pains in the ass by getting up on stage and making us laugh at all that is sacred. After all, what could be more enjoyable than that moment when a genuinely funny comedian makes the kind of crack that compels a whole nation to hold their collective breath and think to themselves in unison, “Oh no you didn’t!”? Here we raise a glass to the top ten most controversial comedians of all time.

10. Andy Kaufman

Kaufman was the king of self-deprecating, ambiguous performances and stunts on live television. The showman and star of Taxi was infamously difficult to work with, frequently ruining takes and exploiting the cameras for his own subversive skits. Indeed, he was so consistently obsessed with seemingly ruining his own reputation that he became blacklisted by countless television studios. Amongst his many stunts, Kaufman infamously decided to punish a live audience at one of his own shows by painstakingly reading aloud a novel from cover to cover until the stalls had emptied in frustration. He also faked a celebrity feud with Jerry Lawler, culminating in an on-screen fight on The David Letterman Show which led to him injuring his neck. Ten years later the whole skit was revealed as a prank. Many even claim that Kaufman faked his own tragic death from cancer in 1984 and is still alive.

9. Lenny Bruce

Lenny Bruce was the father of all comedic controversy. The rising star of the comedy circuit in the 1960s was arrested on obscenity charges countless times following a show in 1964 in which he simply uttered the word ‘cocksucker.’ He was reputedly blacklisted from almost every major comedy venue in the United States and was eventually convicted and ordered to serve four months in a workhouse. His hounding by the feds led to a massive reevaluation of the obscenity laws in the U.S, with Bruce receiving support from such fellow artists as Woody Allen and Bob Dylan. He died of an overdose, aged just 40, and was the first person ever to be granted a posthumous pardon by the State of New York.

8. Richard Pryor

In 1967, Richard Pryor walked onto the stage at a packed out Aladdin Hotel in Las Vegas after having what he described as an instantaneous epiphany, looked into the microphone and asked the audience, “What the fuck am I doing here?” before walking straight off again. Thus began the true career of the first African American to truly take comedy to a new level. Pryor began life as a safe comic selling out shows in safe venues for safe crowds; then he had this ‘moment’ in Las Vegas. What followed were nearly three decades of him holding the torch for controversial and up-front comedy routines directly challenging racial stereotypes and laden with more profanities than a burns victim jumping into a pool of vinegar.

7. Dick Gregory

There are many younger fans of stand-up comedy who may never have heard of Dick Gregory, let alone know of his story, but back in the 1960s he was – quite literally – the first mainstream black comedian to make jokes about the racial issues gripping America at the time. Born in the South, Gregory was not only exceptionally funny but also deeply politically involved, taking an active part in the fledgling Civil Rights movements of the time. His skits, lampooning the Jim Crow laws and the arcane attitude of Southern whites, were not only popular with black audiences, but with white audiences as well.

6. Jon Stewart

‘Controversial’ not because of bad language or any other obvious staples of the average naughty comedian, Stewart has amassed an army of enemies – and an army of fans – through being one of the most intelligent and downright ball-bustin’ left wing political satirists of his generation. One of his more famous moments was his appearance on the political pantomime Crossfire in 2004, wherein – amongst other things – he pleaded with the hosts to cease with their “partisan hackery,” stealing the show and continually attacking its morals for the entirety of his interview. It led to a much publicized rivalry with Tucker Carlson and cemented his place in the annals of political lampooning.

5. Louis C.K.

A man who has a plethora of hilarious routines, and seems totally oblivious to the sensitivity of some of his potential audience, Louis C.K. has managed to rack up plenty of controversy points over the years. Approaching such subjects as killing his 4-year-old, and issuing a – reputedly – ‘drunken’ tweet explicitly attacking Sarah Palin, the comedian has unsurprisingly garnered much media attention. Through it all he’s maintained a large fan-base; google his frankly excellent line, “It’s great being a white male,” and see why.

4. Stephen Colbert

OK, so the left-of-center host of the eponymous Colbert Report may not be an obvious choice in a top ten list of controversial comedians, but we challenge you to watch his appearance at the 2006 White House Correspondents’ Association Dinner – in its entirety – and not come out at the end agreeing with our choice. In the face of almost total awkward silence, Stephen spent his quarter of an hour slot satirizing, undermining and ridiculing the entire Bush administration and half the country’s media, as they all sat there taking it. Although not initially widely picked up by the press, the video footage of the event became an internet phenomenon, leading to Colbert being awarded an award for ‘Ballsiest Comedian of 2006.’

3. Sarah Silverman

Magnificently walking the tightrope between Liberalism and political incorrectness, Silverman has enjoyed a decade of success telling jokes that satirize just about every aspect of American racism. After gaining her big break following a major controversy at the turn of the millennium – in which she extolled the benefits of using casual xenophobia in order to avoid jury duty – she’s managed to make cracks about every sore subject of the last 100 years. The Holocaust, AIDS, 9/11, nothing is too holy to avoid her scathing satire. She’s like a female, girl-next-door South Park, and through her subtle technique of playing devil’s advocate, she has benefited from controversy like no other.

2. George Carlin

Despite sadly no longer being with us, George Carlin’s routines are still some of the most watched clips on the internet, and he enjoys an almost unanimous public and celebrity fan-base. Controversial from the start, he spent his career undermining anyone or anything that dared try and impose a sense of power. His most controversial routine by far was his ‘Seven Words You Can Never Say On Television’ routine from 1972. The skit was a diatribe of profanities – including the deeply unpopular ‘C’ word – in an era when swearing in the media was not exactly looked upon lightly. Carlin was not only arrested for performing it live, it became such a hot topic that it went all the way to the Supreme Court. It was seen as a hallmark for regulations on control over speech within American broadcasting and even now probably isn’t safe for most TV stations.

1. Bill Hicks

One of the true gods of controversial, scathing comedy, Bill Hicks spent his entire short life performing, and pushing the boundaries of sensibility. He was one of the first and only comedians to publicly lampoon the Gulf War, and spent a decade of his career battling censorship issues over such subjects as the Resurrection and the handicapped. Described often as one of the darkest of comics, he even joked about his impending death while dying of cancer in the mid-nineties.